HRP20090265T1 - 1-benzoyl-piperazine derivatives as glycine uptake inhibitors for the treatment of psychoses - Google Patents

1-benzoyl-piperazine derivatives as glycine uptake inhibitors for the treatment of psychoses

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Publication number
HRP20090265T1
HRP20090265T1 HR20090265T HRP20090265T HRP20090265T1 HR P20090265 T1 HRP20090265 T1 HR P20090265T1 HR 20090265 T HR20090265 T HR 20090265T HR P20090265 T HRP20090265 T HR P20090265T HR P20090265 T1 HRP20090265 T1 HR P20090265T1
Authority
HR
Croatia
Prior art keywords
piperazine
nitrobenzoyl
alkyl
fluoro
chloro
Prior art date
Application number
HR20090265T
Other languages
Croatian (hr)
Inventor
Alberati-Giani Daniela
Jolidon Synese
Narquizian Robert
Heinrich Nettekoven Matthias
David Norcross Roger
Pinard Emmanuel
Stalder Henri
Original Assignee
F. Hoffmann - La Roche Ag
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Application filed by F. Hoffmann - La Roche Ag filed Critical F. Hoffmann - La Roche Ag
Publication of HRP20090265T1 publication Critical patent/HRP20090265T1/en

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Abstract

Spojevi formule,naznačeni time, da jeAr supstituirani aril ili nesupstituirani ili supstituirani pirimidin-2-il, [1,3,5]triazin-2-il ili piridin-2-il, i gdje arilne i heteroarilne skupine mogu biti supstituirane s jednim ili više supstituenata izabranih iz skupine koja se sastoji od hidroksi, halogen, CN, (C1-C6)-alkil, (C1-C6)-alkila supstituiranog halogenom, (C1-C6)-alkoksi, (C1-C6)-alkoksi supstituiranog halogenom, NR7R8, C(O)R9 ili SO2R10;R1 je vodik ili (C1-C6)-alkil; R2 je halogen, (C1-C6)-alkil, (C2-C6)-alkenil, gdje vodikov atom može biti zamijenjen s CN, C(O)-R9 ili (C1-C6)-alkilom, ili je (C2-C6)-alkinil, (C1-C6)-alkil supstituiran halogenom, -(CH2)n-(C3-C7)-cikloalkil, -(CH2)n-heterocikloalkil, -C(O)-R9, -(CH2)n-aril ili -(CH2)n-heteroaril s 5 ili 6 članova koji sadrži jedan, dva ili tri heteroatoma izabranih iz skupine koja se sastoji od kisika, sumpora ili dušika gdje su aril, cikloalkil, heterocikloalkil i heteroaril nesupstituirani ili supstituirani s jednim ili više supstituenata izabranih iz skupine koja se sastoji od hidroksi, halogen, (C1-C6)-alkil, (C1-C6)-alkila supstituiranog halogenom ili (C1-C6)-alkoksi; R3, R4 i R6 su neovisno jedan od drugog vodik, hidroksi, halogen, (C1-C6)-alkil ili (C1-C6)-alkoksi; R5 je NO2, CN, C(O)R9, SO2R10 ili NR11R12;R7 i R8 su neovisno jedan od drugog vodik ili (C1-C6)-alkil; R9 je (C1-C6)-alkil, (C3-C6)-cikloalkil, (C1-C6)-alkoksi ili NR7R8;R10 je (C1-C6)-alkil, (C3-C6)-cikloalkil ili NR7R8, uz uvjet da je jedan od R7 ili R8 (C1-C6)-alkil; R11 i R12 su neovisno jedan od drugog vodik ili tvore heteroarilnu skupinu s 5 članova zajedno s N-atomom na koji su pričvršćeni; n je 0,1 ili 2; i njihove farmaceutski prihvatljive soli, uz uvjet da su1-(2-klor-5-nitrobenzoil)-4-(4-metoksifenil)-piperazin, 1-(2-klor-5-nitrobenzoil)-4-(4-klorfenil)-piperazin, 1-(2-fluor-5-nitrobenzoil)-4-[2-fluor-4-(1-oksobutil)fenil]-piperazin, 1-(2-fluor-5-nitrobenzoil)-4-[2-fluor-4-(1-oksopropil)fenil]-piperazin, 1-(2-klor-5-nitrobenzoil)-4-(2,3-dimetilfenil)-piperazin, 1-(2-klor-5-nitrobenzoil)-4-(3-klorofenil)-piperazin, 1-(2-klor-5-nitrobenzoil)-4-(2-etoksifenil)-piperazin, 1-(4-acetil-2-fluorofenil)-4-(2-fluor-5-nitrobenzoil)-piperazin, 1-(2-klor-5-nitrobenzoil)-4-(4-fluorofenil)-piperazin, 1-(2-klor-5-nitrobenzoil)-4-(2-metoksifenil)-piperazin, i1-(4-acetil-2-fluor-5-metilfenil)-4-(2-fluor-5-nitrobenzoil)-piperazin1-(2-klor-5-nitrobenzoil)-4-(2-piridinil)-piperazin, 1-(4-acetil-2-fluorofenil)-4-[2-(4-morfolinil)-5-nitrobenzoil]-piperazin, 1-[2-fluor-4-(1-oksopropil)fenil]-4-[2-(4-morfolinil)-5-nitrobenzoil]-piperazin, 1-[2-fluor-4-(1-oksopropil)fenil]-4-[2-(4-metil-1-piperazinil)-5-nitrobenzoil]-piperazin, 1-[2-fluor-4-(1-oksopropil)fenil]-4-[2-(4-metil-1-piperidinil)-5-nitrobenzoil]-piperazin, 1-[2-fluor-4-(1-oksopropil)fenil]-4-[5-nitro-2-(1-pirolidinil)benzoil]-piperazin, 1-[2-fluor-4-(1-oksopropil)fenil]-4-[5-nitro-2-(1-piperidinil)benzoil]-piperazin, 1-(4-metoksifenil)-4-[2-(4-morfolinil)-5-nitrobenzoil]-piperazCompounds of formula wherein Ar is substituted aryl or unsubstituted or substituted pyrimidin-2-yl, [1,3,5] triazin-2-yl or pyridin-2-yl, and wherein the aryl and heteroaryl groups may be substituted with one or more substituents selected from the group consisting of hydroxy, halogen, CN, (C1-C6) -alkyl, (C1-C6) -alkyl substituted by halogen, (C1-C6) -alkoxy, (C1-C6) -alkoxy substituted halogen, NR7R8, C (O) R9 or SO2R10, R1 is hydrogen or (C1-C6) -alkyl; R 2 is halogen, (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyl, where the hydrogen atom may be replaced by CN, C (O) -R 9 or (C 1 -C 6) -alkyl, or is (C 2 -C 6) ) -alkynyl, (C1-C6) -alkyl substituted by halogen, - (CH2) n- (C3-C7) -cycloalkyl, - (CH2) n-heterocycloalkyl, -C (O) -R9, - (CH2) n- aryl or - (CH2) n-heteroaryl of 5 or 6 members containing one, two or three heteroatoms selected from the group consisting of oxygen, sulfur or nitrogen wherein aryl, cycloalkyl, heterocycloalkyl and heteroaryl are unsubstituted or substituted by one or more substituents selected from the group consisting of hydroxy, halogen, (C1-C6) -alkyl, (C1-C6) -alkyl substituted by halogen or (C1-C6) -alkoxy; R 3, R 4 and R 6 are independently hydrogen, hydroxy, halogen, (C 1 -C 6) -alkyl or (C 1 -C 6) -alkoxy; R 5 is NO 2, CN, C (O) R 9, SO 2 R 10 or NR 11 R 12, R 7 and R 8 are independently hydrogen or (C 1 -C 6) -alkyl; R9 is (C1-C6) -alkyl, (C3-C6) -cycloalkyl, (C1-C6) -alkoxy or NR7R8, R10 is (C1-C6) -alkyl, (C3-C6) -cycloalkyl or NR7R8, provided that one of R7 or R8 is (C1-C6) -alkyl; R 11 and R 12 are independently hydrogen or form a 5-membered heteroaryl group together with the N-atom to which they are attached; n is 0, 1 or 2; and pharmaceutically acceptable salts thereof, provided that they are 1- (2-chloro-5-nitrobenzoyl) -4- (4-methoxyphenyl) -piperazine, 1- (2-chloro-5-nitrobenzoyl) -4- (4-chlorophenyl) -piperazine, 1- (2-fluoro-5-nitrobenzoyl) -4- [2-fluoro-4- (1-oxobutyl) phenyl] -piperazine, 1- (2-fluoro-5-nitrobenzoyl) -4- [2 -fluoro-4- (1-oxopropyl) phenyl] -piperazine, 1- (2-chloro-5-nitrobenzoyl) -4- (2,3-dimethylphenyl) -piperazine, 1- (2-chloro-5-nitrobenzoyl) -4- (3-chlorophenyl) -piperazine, 1- (2-chloro-5-nitrobenzoyl) -4- (2-ethoxyphenyl) -piperazine, 1- (4-acetyl-2-fluorophenyl) -4- (2- Fluoro-5-nitrobenzoyl) -piperazine, 1- (2-chloro-5-nitrobenzoyl) -4- (4-fluorophenyl) -piperazine, 1- (2-chloro-5-nitrobenzoyl) -4- (2-methoxyphenyl) -piperazine, 1- (4-acetyl-2-fluoro-5-methylphenyl) -4- (2-fluoro-5-nitrobenzoyl) -piperazine-1 (2-chloro-5-nitrobenzoyl) -4- (2-pyridinyl) -piperazine, 1- (4-acetyl-2-fluorophenyl) -4- [2- (4-morpholinyl) -5-nitrobenzoyl] -piperazine, 1- [2-fluoro-4- (1-oxopropyl) phenyl] - 4- [2- (4-morpholinyl) -5-nitrobenzoyl] -piperazine, 1- [2-fluoro-4- (1-oxopropyl) phenyl] -4- [2- (4-methyl-1-piperazinyl) - 5-nitro benzoyl] -piperazine, 1- [2-fluoro-4- (1-oxopropyl) phenyl] -4- [2- (4-methyl-1-piperidinyl) -5-nitrobenzoyl] -piperazine, 1- [2-fluoro -4- (1-oxopropyl) phenyl] -4- [5-nitro-2- (1-pyrrolidinyl) benzoyl] -piperazine, 1- [2-fluoro-4- (1-oxopropyl) phenyl] -4- [ 5-nitro-2- (1-piperidinyl) benzoyl] -piperazine, 1- (4-methoxyphenyl) -4- [2- (4-morpholinyl) -5-nitrobenzoyl] -piperazine

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